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Cheap flights from New York to Chicago from $106

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 17/12. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
27 Dec — 3 Jan1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 64 days in advance, depart on a Tuesday or Thursday and return on a Thursday

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Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 November 2025.

Mon 29/1206:55EWR - ORD
Nonstop2h 36mSpirit Airlines
Thu 8/110:39ORD - EWR
1 stop12h 13mSpirit Airlines
Deal found 25/11$180
Tue 16/1221:57EWR - ORD
Nonstop2h 35mUnited Airlines
Thu 18/1206:00ORD - EWR
Nonstop2h 10mUnited Airlines
Deal found 25/11$211
Wed 3/1208:00EWR - ORD
Nonstop2h 48mUnited Airlines
Thu 18/1206:00ORD - EWR
Nonstop2h 10mUnited Airlines
Deal found 25/11$220
Wed 3/1221:57EWR - ORD
Nonstop2h 35mUnited Airlines
Mon 8/1221:08ORD - EWR
Nonstop2h 05mUnited Airlines
Deal found 26/11$229
Thu 4/1207:07EWR - ORD
Nonstop2h 58mAmerican Airlines
Mon 8/1219:27ORD - EWR
Nonstop2h 14mAmerican Airlines
Deal found 26/11$231
Sun 14/1209:00EWR - ORD
Nonstop2h 44mUnited Airlines
Thu 18/1221:10ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 26/11$237
Sun 14/1209:00EWR - ORD
Nonstop2h 44mUnited Airlines
Mon 15/1213:36ORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 25/11$240
Mon 8/1214:25EWR - ORD
Nonstop2h 39mUnited Airlines
Fri 12/1219:40ORD - EWR
Nonstop2h 22mUnited Airlines
Deal found 25/11$246
Tue 16/1211:30EWR - ORD
Nonstop2h 39mUnited Airlines
Mon 22/1221:10ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 25/11$249
Wed 10/1215:30EWR - ORD
Nonstop2h 40mUnited Airlines
Tue 6/119:42ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 25/11$252
Tue 16/1209:55EWR - ORD
1 stop11h 06mSpirit Airlines
Thu 18/1209:34ORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 25/11$257
Fri 12/1221:57EWR - ORD
Nonstop2h 35mUnited Airlines
Mon 22/1206:00ORD - EWR
Nonstop2h 10mUnited Airlines
Deal found 26/11$258

Cheap flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 27 November 2025.

Round-trip from

$166

One-way from

$106

Popular in

August

Cheapest in

January

Average price

$363

Good round-trip deal

$2,143 or less

Good one-way deal

$106 or less
Frontier
  • Frontier
  • 9/1-16/1
  • 1 total stop
  • 10h 09m total
  • New York to Chicago
Search Deals
United Airlines
  • United Airlines
  • 17/12
  • Nonstop
  • 2h 47m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($50 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from New York (NYC) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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Cheapflights Fare Finder

 
Customise your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 27 November 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 6/2

05:00-17:52

1 stop13h 52m

Chicago O'Hare Intl

Mon 9/2

20:22-10:57

1 stop13h 35m

$191

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 30/1

12:42-14:28

Nonstop2h 46m

Chicago O'Hare Intl

Sun 1/2

06:05-09:15

Nonstop2h 10m

$241

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 7/12

06:00-07:42

Nonstop2h 42m

Chicago O'Hare Intl

Sun 14/12

19:40-23:02

Nonstop2h 22m

$246

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 4/2

09:47-13:13

1 stop4h 26m

Chicago O'Hare Intl

Sat 7/2

10:35-16:02

1 stop4h 27m

$272

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 7/2

14:30-19:21

1 stop5h 51m

Chicago O'Hare Intl

Wed 11/2

18:00-23:13

1 stop4h 13m

$272

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 3/2

09:47-13:13

1 stop4h 26m

Chicago O'Hare Intl

Mon 9/2

17:35-23:13

1 stop4h 38m

$272

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 7/2

06:00-10:25

1 stop5h 25m

Chicago O'Hare Intl

Mon 9/2

17:35-23:13

1 stop4h 38m

$272

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 7/2

06:00-10:25

1 stop5h 25m

Chicago O'Hare Intl

Sat 7/2

17:35-23:13

1 stop4h 38m

$272

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 5/2

09:47-13:13

1 stop4h 26m

Chicago O'Hare Intl

Sat 7/2

06:50-12:09

1 stop4h 19m

$272

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 2/2

09:47-13:13

1 stop4h 26m

Chicago O'Hare Intl

Mon 2/2

17:35-23:13

1 stop4h 38m

$272

Flights are sorted by cheapest return flights first.

Deals found on 26/11

Showing 1-10 of 21 results
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

How far ahead should I book a flight from New York to Chicago?

Use this chart to determine the optimal time to book a return flight from New York to Chicago. Price data was last updated on 21 November 2025.

The best time to book flights from New York to Chicago is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from New York to Chicago?

Currently, May is the cheapest month in which you can book a flight from New York to Chicago (average of $85). Flying from New York to Chicago in July is currently the most expensive (average of $194). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 27 November 2025.

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 85% versus a flight in the afternoon.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 27 November 2025.

The most flights from NYC to CHI are scheduled on a Wednesday (186 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (38 on average).

How often are flights from New York to Chicago delayed?

About 15% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 159 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, TezJet have had the lowest number of delays on this route, with no flights being classified as delayed.

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New York to Chicago?

    Airlines like Spirit Airlines, United Airlines, and Delta fly from New York to Chicago in about 2h 46m. The time it takes to get you to your destination can typically vary by up to 11h 06m. New York and Chicago are separated by a distance of 1152 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Atlas Air (100%), Finnair (100%), Gulf Air (88%).

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, May is the cheapest month in which you can book a flight from New York to Chicago (average of $85). Flying from New York to Chicago in July is currently the most expensive (average of $194). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights

Fly with Cheapflights

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How does Cheapflights help users find flights from New York to Chicago?

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from New York to Chicago with no change fees?

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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